Best for The beach, romance, watersports, partying, culture and history, nature, escapism.

The Caribbean’s most fascinating country: a heady mix of faded Spanish colonial cities, sputtering Fifties Cadillacs, wonderful live music, world-class cigars and an arcane communist system. On the downside, often things don’t work as they should or go to plan, and the service in hotels and the food, though improving, are not on a par with other Caribbean destinations.

Holiday options include city breaks to sultry Havana (lots of cultural offerings and great nightlife) and touring, either in a guided group or self-drive. The beautiful tobacco heartlands of Viñales, the crumbling colonial town of Trinidad, and sights related to Che Guevara and the revolution are highlights. Independent travellers can have rewarding, inexpensive adventures staying with Cubans in their homes (see cubacasas.net) and eating in their houses in private restaurants, called paladares.

Though Thomson has stopped offering packages to Cuba, stay-put beach packages are still big business, and many of the beaches are fantastic, including at Varadero, the biggest resort. However, with so much else to enjoy in Cuba, you may regret holing up in an all-inclusive hotel for your whole trip. Consider a Havana/Varadero two-centre stay – other resorts are more isolated.

Timing advice The world-class International Havana Jazz Festival takes place from December 13-20, 2014, and Santiago de Cuba’s carnival, the island’s most famous, in late July.